Within Japanese ELT, private conversation ("eikaiwa") schools are commonly viewed as the bottom rung of the professional ladder. In contrast to "eikaiwa's" marginalized position, language teaching in university is regarded as the pinnacle of the field's professional hierarchy (Nagatomo, 2016). The aim of this paper is to examine first-hand perspectives of teachers who have transitioned between these two 'spheres of experience' (Zittoun, 2006) and analyze perspectives on each context's pedagogical constraints and affordances. Drawing on Zittoun's sociocultural framework related to life transitions, an investigation of the lived experiences of eleven teachers was conducted. This explorative study focused on changes in skills and knowledge, identity, and personal meanings that stemmed from moving from "eikaiwa" to university teaching as well as cognitive and social resources that mediated the transition. Teachers revealed that "eikaiwa" teaching provided them with experiences that contributed to their pedagogical skillset and evolving teacher beliefs. Conversely, university teaching afforded enhanced professional identity due to factors such as increased teacher autonomy and authority in the classroom. This study supports a nuanced view of different teaching contexts that recognizes diverse affordances and constraints rather than subscribing to a linear, hierarchical view of certain ELT settings.